Water → (+/-)-1-(Benzofuran-6-yloxy)-4-pyridin-3-yl-butan-2-ol

HRID 1856688ノート

反応式

HRID 1856688 の反応式
Cl[CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[OH:13][C:14]1[CH:22]=[CH:21][C:17]2[CH:18]=[CH:19][O:20][C:16]=2[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[O:20]1[C:16]2[CH:15]=[C:14]([O:13][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[CH:22]=[CH:21][C:17]=2[CH:18]=[CH:19]1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 1288446-HydroxybenzofuranHCID 22465338HCID 22465338、化合物

生成物 1

HCID 22132417(+/-)-1-(Benzofuran-6-yloxy)-4-pyridin-3-yl-butan-2-ol収率 24.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
120 °C

実験手順

##STR16## (±)-α-(Chloromethyl)-3-pyridinepropanol (0.339 g, Example 2a)) was dissolved in anhydrous N,N-dimethylformamide (5 ml) and added to a suspension of 6-hydroxybenzofuran (0.245 g, Bull. Soc. Chim. Fr., 1973, 2355) and cesium carbonate (0.596 g) in anhydrous N,N-dimethylformamide (5 ml) which had been heated previously for one hour at 120° C. The mixture was then heated at 120° C. for 7 hours before being cooled to room temperature. The mixture was then poured into water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1) and recrystallised from ethyl acetate:hexane to give the title compound (0.129 g).

後処理

  1. temperatureThe mixture was then heated at 120° C. for 7 hours
  2. temperaturebefore being cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography over silica eluting with dichloromethane:ethanol (19:1)
  9. customrecrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-af602329fe954273a4521369291998f5
出典データセット
uspto-grants-2000_11
特許番号
US06143751

反応ノート

読み込み中…